CZ281049B6 - Antipsychoticky účinné benzodioxanové deriváty - Google Patents
Antipsychoticky účinné benzodioxanové deriváty Download PDFInfo
- Publication number
- CZ281049B6 CZ281049B6 CS921823A CS182392A CZ281049B6 CZ 281049 B6 CZ281049 B6 CZ 281049B6 CS 921823 A CS921823 A CS 921823A CS 182392 A CS182392 A CS 182392A CZ 281049 B6 CZ281049 B6 CZ 281049B6
- Authority
- CZ
- Czechia
- Prior art keywords
- dihydro
- mmol
- carbon atoms
- methanamine
- pharmaceutically acceptable
- Prior art date
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- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title claims description 4
- 230000000561 anti-psychotic effect Effects 0.000 title abstract description 6
- 230000001747 exhibiting effect Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 105
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- -1 alkanamido Chemical group 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 32
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
- JHNURUNMNRSGRO-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-3-ylmethanamine Chemical group C1=CC=C2OC(CN)COC2=C1 JHNURUNMNRSGRO-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- FAEYVNUUDKJBGP-UHFFFAOYSA-N 2-[[3-(3-aminophenoxy)propylamino]methyl]-2,3-dihydro-1,4-benzodioxin-6-ol Chemical compound NC1=CC=CC(OCCCNCC2OC3=CC=C(O)C=C3OC2)=C1 FAEYVNUUDKJBGP-UHFFFAOYSA-N 0.000 claims description 2
- KDDBDNPSJMZIKH-UHFFFAOYSA-N 3-[3-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methylamino]propoxy]aniline Chemical compound NC1=CC=CC(OCCCNCC2OC3=CC(F)=CC=C3OC2)=C1 KDDBDNPSJMZIKH-UHFFFAOYSA-N 0.000 claims description 2
- RRTWKFLXRKVQID-UHFFFAOYSA-N 3-[3-[(6-methoxy-2,3-dihydro-1,4-benzodioxin-3-yl)methylamino]propoxy]aniline Chemical compound O1C2=CC(OC)=CC=C2OCC1CNCCCOC1=CC=CC(N)=C1 RRTWKFLXRKVQID-UHFFFAOYSA-N 0.000 claims description 2
- XQRSLRUXPXVCRY-UHFFFAOYSA-N 3-[[3-(3-aminophenoxy)propylamino]methyl]-2,3-dihydro-1,4-benzodioxin-6-ol Chemical compound NC1=CC=CC(OCCCNCC2OC3=CC(O)=CC=C3OC2)=C1 XQRSLRUXPXVCRY-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- LMBFNEOWVJJHPC-UHFFFAOYSA-N 3-[3-[(6,7-dimethoxy-2,3-dihydro-1,4-benzodioxin-3-yl)methylamino]propoxy]aniline Chemical compound O1C=2C=C(OC)C(OC)=CC=2OCC1CNCCCOC1=CC=CC(N)=C1 LMBFNEOWVJJHPC-UHFFFAOYSA-N 0.000 claims 1
- KJGCUQLKPDHNKF-UHFFFAOYSA-N C1OC2=CC3=C(C=C2O1)OC(C(O3)CN)OC4=CC=CC(=C4)N Chemical compound C1OC2=CC3=C(C=C2O1)OC(C(O3)CN)OC4=CC=CC(=C4)N KJGCUQLKPDHNKF-UHFFFAOYSA-N 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 abstract description 6
- 239000000164 antipsychotic agent Substances 0.000 abstract description 5
- 239000000935 antidepressant agent Substances 0.000 abstract description 4
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- 208000015114 central nervous system disease Diseases 0.000 abstract description 3
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- 238000000921 elemental analysis Methods 0.000 description 51
- 239000002904 solvent Substances 0.000 description 51
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- 239000012299 nitrogen atmosphere Substances 0.000 description 32
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- 239000003480 eluent Substances 0.000 description 27
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 24
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- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- FUAXXSWWKCVWMD-UHFFFAOYSA-N n,n-dipropyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N(CCC)CCC)CCCC2=C1 FUAXXSWWKCVWMD-UHFFFAOYSA-N 0.000 description 1
- YJPHXPWNPFQMGC-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)ethanamine Chemical compound C1=CC=C2OC(CNCC)COC2=C1 YJPHXPWNPFQMGC-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 210000001009 nucleus accumben Anatomy 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical class O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical group C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 208000012201 sexual and gender identity disease Diseases 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
- Insulators (AREA)
- Light Receiving Elements (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/719,882 US5166367A (en) | 1991-06-21 | 1991-06-21 | Antipsychotic benzodioxan derivatives |
| US07/719,887 US5126366A (en) | 1991-06-21 | 1991-06-21 | Aminophenoxyalkyl derivatives of benzodioxan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ182392A3 CZ182392A3 (en) | 1993-01-13 |
| CZ281049B6 true CZ281049B6 (cs) | 1996-06-12 |
Family
ID=27110156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS921823A CZ281049B6 (cs) | 1991-06-21 | 1992-06-15 | Antipsychoticky účinné benzodioxanové deriváty |
Country Status (19)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5235055A (en) * | 1992-09-02 | 1993-08-10 | American Home Products Corporation | Antipsychotic quinoline derivatives of benzodioxanmethylamine |
| DE10029371A1 (de) * | 2000-06-20 | 2002-01-03 | Merck Patent Gmbh | Heterocyclische Aminoalkylpyridinderivate als Psychopharmaka |
| EP1748995B1 (en) * | 2004-05-05 | 2010-02-24 | F. Hoffmann-La Roche AG | Arylsulfonyl benzodioxanes useful for modulation the 5-ht6 receptor, the 5-ht2areceptor or both |
| KR102021281B1 (ko) * | 2018-05-25 | 2019-09-16 | 한국 한의학 연구원 | 프락신을 유효성분으로 포함하는 우울증 및 불안장애 예방, 개선 또는 치료용 조성물 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1096301A (en) | 1963-06-20 | 1967-12-29 | Ward Blenkinsop & Co Ltd | 1,4-benzodioxane derivatives |
| US4701456A (en) * | 1984-09-19 | 1987-10-20 | Warner-Lambert Company | Aminoalkoxybenzopyranones as antipsychotic and anxiolytic agents |
-
1992
- 1992-05-05 TW TW081103485A patent/TW203047B/zh active
- 1992-06-09 IL IL10213792A patent/IL102137A/en not_active IP Right Cessation
- 1992-06-15 CZ CS921823A patent/CZ281049B6/cs unknown
- 1992-06-17 ES ES92305535T patent/ES2076691T3/es not_active Expired - Lifetime
- 1992-06-17 JP JP04157853A patent/JP3095533B2/ja not_active Expired - Fee Related
- 1992-06-17 EP EP92305535A patent/EP0520674B1/en not_active Expired - Lifetime
- 1992-06-17 DK DK92305535.4T patent/DK0520674T3/da active
- 1992-06-17 AT AT92305535T patent/ATE126515T1/de not_active IP Right Cessation
- 1992-06-17 DE DE69204117T patent/DE69204117T2/de not_active Expired - Fee Related
- 1992-06-18 NZ NZ243194A patent/NZ243194A/en unknown
- 1992-06-18 FI FI922880A patent/FI922880A7/fi unknown
- 1992-06-19 HU HU9202060A patent/HUT61739A/hu unknown
- 1992-06-19 BR BR929202321A patent/BR9202321A/pt not_active Application Discontinuation
- 1992-06-19 RU SU925011900A patent/RU2056417C1/ru active
- 1992-06-19 KR KR1019920010660A patent/KR930000496A/ko not_active Withdrawn
- 1992-06-19 PH PH44535A patent/PH30817A/en unknown
- 1992-06-22 MX MX9203109A patent/MX9203109A/es unknown
- 1992-06-22 AU AU18426/92A patent/AU644743B2/en not_active Ceased
-
1995
- 1995-11-16 GR GR950403227T patent/GR3018111T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0520674T3 (da) | 1996-01-08 |
| DE69204117D1 (de) | 1995-09-21 |
| PH30817A (en) | 1997-10-17 |
| FI922880L (fi) | 1992-12-22 |
| IL102137A0 (en) | 1993-01-14 |
| HU9202060D0 (en) | 1992-09-28 |
| FI922880A7 (fi) | 1992-12-22 |
| EP0520674A1 (en) | 1992-12-30 |
| TW203047B (enrdf_load_stackoverflow) | 1993-04-01 |
| JPH05194481A (ja) | 1993-08-03 |
| ES2076691T3 (es) | 1995-11-01 |
| DE69204117T2 (de) | 1996-03-14 |
| MX9203109A (es) | 1993-06-01 |
| FI922880A0 (fi) | 1992-06-18 |
| EP0520674B1 (en) | 1995-08-16 |
| NZ243194A (en) | 1993-10-26 |
| AU1842692A (en) | 1992-12-24 |
| BR9202321A (pt) | 1993-01-19 |
| JP3095533B2 (ja) | 2000-10-03 |
| AU644743B2 (en) | 1993-12-16 |
| IL102137A (en) | 1996-07-23 |
| KR930000496A (ko) | 1993-01-15 |
| GR3018111T3 (en) | 1996-02-29 |
| ATE126515T1 (de) | 1995-09-15 |
| CZ182392A3 (en) | 1993-01-13 |
| HUT61739A (en) | 1993-03-01 |
| RU2056417C1 (ru) | 1996-03-20 |
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